Ammonium Hydroxide → HCID 22917178, compound

HRID 1984834Notes

Reaction equation

HRID 1984834 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=O)[NH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].[NH4+].[OH-].O=P(Cl)(Cl)[Cl:23]>>[CH2:1]([O:3][C:4]([C:6]1[C:15]([Cl:23])=[N:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 22917218HCID 22917218, compound

Product 1

HCID 22917178HCID 22917178, compound

Conditions

Temperature
100 °C

Procedure

6-Methoxy-3-oxo-3,4-dihydro-quinoxaline-2-carboxylic acid ethyl ester (5.2 g, 20.9 mmol) was suspended in 75 mL of POCl3 and resulting mixture heated to 100° C. for 1 h. The reaction mixture was poured onto 500 mL of ice-water and the pH of the solution adjusted to 3 with conc. NH4OH. Mixture was extracted twice with 300 mL of EtOAc. The combined organic layers were dried over Na2SO4 and evaporated to give the 3-chloro-6-methoxy-quinoxaline-2-carboxylic acid ethyl ester (4.6 g).

Workup

  1. customresulting mixture
  2. extractionMixture was extracted twice with 300 mL of EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-0b65a707237643418df78014baf885c6
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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